Ethyl 9-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate → 2-(3-Hydroxyphenyl)-8-oxo-9-(piperidin-4-YL)-8,9-dihydro-7H-purine-6-carboxamide

HRID 391707Notes

Reaction equation

HRID 391707 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22](=[O:23])[NH:21][C:20]3[C:15]2=[N:16][C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[N:18][C:19]=3[C:24]([O:26]CC)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:36]C1C(C(OCC)=O)=NC(C2C=CC=C(O)C=2)=NC=1NC1CCN(C(OC(C)(C)C)=O)CC1>ClCCl>[OH:35][C:31]1[CH:30]=[C:29]([C:17]2[N:16]=[C:15]3[C:20]([NH:21][C:22](=[O:23])[N:14]3[CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[C:19]([C:24]([NH2:36])=[O:26])[N:18]=2)[CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 57474836Ethyl 9-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylateHCID 57474837Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate

Product 1

HCID 574748382-(3-Hydroxyphenyl)-8-oxo-9-(piperidin-4-YL)-8,9-dihydro-7H-purine-6-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 9-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-6-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate (0.120 g, 0.260 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.425 g, 2.62 mmol) in dichloromethane (10 mL) were reacted according to General Procedure F and purified via biotage chromatography (0-70% EtOAc in hexanes) to afford the title compound (0.050 g, 19%). MS (ESI) m/z 484.3 [M+1]+.

Workup

  1. custompurified via biotage chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-797072a03a194dd18b70c12c58743f75
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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